# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436749'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Cu N O6'
_chemical_formula_weight         335.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5973(6)
_cell_length_b                   8.1060(6)
_cell_length_c                   12.4901(12)
_cell_angle_alpha                89.576(3)
_cell_angle_beta                 86.095(2)
_cell_angle_gamma                69.787(2)
_cell_volume                     720.03(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.540
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_T_max  0.881

_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24178
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2943
_reflns_number_gt                2555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.1081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2943
_refine_ls_number_parameters     190
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1231(3) -0.2441(3) 0.29266(17) 0.0273(5) Uani 1 1 d . U . . .
C2 C 0.2829(3) -0.3270(3) 0.36345(17) 0.0269(5) Uani 1 1 d . U . . .
C3 C 0.2734(3) -0.4511(3) 0.43563(17) 0.0273(5) Uani 1 1 d . U . . .
H3 H 0.1687 -0.4860 0.4401 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4431(3) -0.2751(3) 0.35503(19) 0.0330(5) Uani 1 1 d . U . . .
H4 H 0.4505 -0.1926 0.3044 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4210(3) -0.5278(3) 0.50397(16) 0.0243(4) Uani 1 1 d . U . . .
C6 C 0.5861(3) -0.3444(3) 0.42021(18) 0.0318(5) Uani 1 1 d . U . . .
H6 H 0.6893 -0.3072 0.4147 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1833(3) -0.3225(3) -0.02161(19) 0.0329(5) Uani 1 1 d . U . . .
H7A H 0.0694 -0.3502 -0.0086 0.040 Uiso 1 1 calc R U . . .
H7B H 0.2758 -0.3923 0.0257 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2582(3) -0.3619(3) -0.1383(2) 0.0361(5) Uani 1 1 d . U . . .
H8A H 0.3871 -0.3647 -0.1461 0.043 Uiso 1 1 calc R U . . .
H8B H 0.2572 -0.4766 -0.1592 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2593(3) -0.1761(3) -0.2951(2) 0.0373(6) Uani 1 1 d . U . . .
H9A H 0.1781 -0.1020 -0.3462 0.045 Uiso 1 1 calc R U . . .
H9B H 0.3401 -0.2819 -0.3331 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3799(3) -0.0806(4) -0.2537(2) 0.0457(7) Uani 1 1 d . U . . .
H10A H 0.4723 -0.1601 -0.2100 0.055 Uiso 1 1 calc R U . . .
H10B H 0.4473 -0.0481 -0.3142 0.055 Uiso 1 1 calc R U . . .
C11 C 0.0037(3) -0.2866(3) -0.26244(19) 0.0340(5) Uani 1 1 d . U . . .
H11A H 0.0717 -0.3927 -0.3042 0.041 Uiso 1 1 calc R U . . .
H11B H -0.0639 -0.1975 -0.3115 0.041 Uiso 1 1 calc R U . . .
C12 C -0.1358(3) -0.3238(3) -0.1830(2) 0.0385(6) Uani 1 1 d . U . . .
H12A H -0.2289 -0.3532 -0.2205 0.046 Uiso 1 1 calc R U . . .
H12B H -0.0719 -0.4224 -0.1387 0.046 Uiso 1 1 calc R U . . .
N008 N 0.1408(2) -0.2254(2) -0.21014(14) 0.0270(4) Uani 1 1 d . U . . .
O1 O 0.1489(2) -0.1327(2) 0.22730(12) 0.0315(4) Uani 1 1 d . U . . .
O2 O -0.0185(2) -0.2863(2) 0.30348(15) 0.0441(5) Uani 1 1 d . U . . .
O1W O -0.4566(3) -0.2160(3) 0.0426(2) 0.0462(5) Uani 1 1 d . . . . .
O3 O 0.1455(2) -0.14130(19) -0.00263(11) 0.0260(3) Uani 1 1 d . U . . .
O4 O 0.2786(2) 0.0715(2) -0.19257(14) 0.0368(4) Uani 1 1 d . U . . .
H4A H 0.2111 0.1453 -0.2312 0.055 Uiso 1 1 calc R U . . .
O5 O -0.2239(2) -0.1711(2) -0.11812(14) 0.0408(4) Uani 1 1 d . U . . .
Cu1 Cu 0.00123(3) 0.00840(3) 0.11616(2) 0.02337(10) Uani 1 1 d . U . . .
H1W H -0.423(4) -0.174(4) 0.090(3) 0.053(11) Uiso 1 1 d . . . . .
H2W H -0.555(5) -0.174(5) 0.038(3) 0.062(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.235(3) . ?
C1 O1 1.269(3) . ?
C1 C2 1.510(3) . ?
C2 C3 1.363(3) . ?
C2 C4 1.416(3) . ?
C3 C5 1.419(3) . ?
C4 C6 1.361(3) . ?
C5 C6 1.411(3) 2_646 ?
C5 C5 1.417(4) 2_646 ?
C6 C5 1.411(3) 2_646 ?
C7 O3 1.414(3) . ?
C7 C8 1.522(3) . ?
C8 N008 1.496(3) . ?
C9 N008 1.486(3) . ?
C9 C10 1.506(4) . ?
C10 O4 1.404(3) . ?
C11 N008 1.487(3) . ?
C11 C12 1.508(3) . ?
C12 O5 1.416(3) . ?
N008 Cu1 2.0452(18) 2 ?
O1 Cu1 1.9482(14) . ?
O3 Cu1 1.9395(14) . ?
O3 Cu1 1.9434(14) 2 ?
Cu1 O3 1.9434(14) 2 ?
Cu1 N008 2.0453(18) 2 ?
Cu1 Cu1 2.9076(6) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 126.1(2) . . ?
O2 C1 C2 119.08(19) . . ?
O1 C1 C2 114.77(19) . . ?
C3 C2 C4 119.9(2) . . ?
C3 C2 C1 120.3(2) . . ?
C4 C2 C1 119.8(2) . . ?
C2 C3 C5 120.9(2) . . ?
C6 C4 C2 120.8(2) . . ?
C6 C5 C5 119.4(2) 2_646 2_646 ?
C6 C5 C3 122.0(2) 2_646 . ?
C5 C5 C3 118.6(2) 2_646 . ?
C4 C6 C5 120.4(2) . 2_646 ?
O3 C7 C8 107.22(18) . . ?
N008 C8 C7 110.74(18) . . ?
N008 C9 C10 114.1(2) . . ?
O4 C10 C9 113.9(2) . . ?
N008 C11 C12 112.83(19) . . ?
O5 C12 C11 108.01(19) . . ?
C9 N008 C11 108.57(17) . . ?
C9 N008 C8 111.41(18) . . ?
C11 N008 C8 111.68(18) . . ?
C9 N008 Cu1 108.72(14) . 2 ?
C11 N008 Cu1 109.42(13) . 2 ?
C8 N008 Cu1 106.98(13) . 2 ?
C1 O1 Cu1 133.49(14) . . ?
C7 O3 Cu1 129.48(13) . . ?
C7 O3 Cu1 108.89(13) . 2 ?
Cu1 O3 Cu1 96.98(6) . 2 ?
O3 Cu1 O3 83.02(6) . 2 ?
O3 Cu1 O1 95.40(6) . . ?
O3 Cu1 O1 177.92(6) 2 . ?
O3 Cu1 N008 162.05(7) . 2 ?
O3 Cu1 N008 84.79(7) 2 2 ?
O1 Cu1 N008 97.05(7) . 2 ?
O3 Cu1 Cu1 41.56(4) . 2 ?
O3 Cu1 Cu1 41.46(4) 2 2 ?
O1 Cu1 Cu1 136.94(5) . 2 ?
N008 Cu1 Cu1 125.03(5) 2 2 ?

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.086

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436750'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H27 Cu N2 O9'
_chemical_formula_weight         430.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2907(5)
_cell_length_b                   13.3305(6)
_cell_length_c                   15.2281(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.358(2)
_cell_angle_gamma                90
_cell_volume                     1800.11(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.264
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_T_max  0.881

_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60810
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         32.156
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6297
_reflns_number_gt                4912
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+2.1168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6297
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.19867(3) 0.21247(2) 0.77426(2) 0.02765(10) Uani 1 1 d . . . . .
O1 O 0.1308(2) 0.32573(13) 0.68980(11) 0.0308(4) Uani 1 1 d . . . . .
O2 O 0.1969(3) 0.26287(16) 0.57121(14) 0.0447(5) Uani 1 1 d . . . . .
O3 O -0.2672(3) 0.41314(15) 0.61906(17) 0.0440(5) Uani 1 1 d . . . . .
H3 H -0.2455 0.4728 0.6261 0.066 Uiso 1 1 calc R U . . .
O4 O -0.1772(2) 0.27959(13) 0.56724(15) 0.0380(4) Uani 1 1 d . . . . .
O6 O 0.2914(2) 0.10031(17) 0.85834(16) 0.0476(5) Uani 1 1 d . . . . .
C1 C 0.1364(3) 0.32704(17) 0.60782(15) 0.0273(4) Uani 1 1 d . . . . .
C2 C 0.0632(2) 0.41636(16) 0.55154(14) 0.0228(4) Uani 1 1 d . . . . .
C3 C -0.0881(2) 0.43836(15) 0.53867(14) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.1506(2) 0.47748(16) 0.51360(14) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.2518 0.4622 0.5231 0.029 Uiso 1 1 calc R U . . .
N1 N 0.4100(3) 0.2686(2) 0.8171(2) 0.0501(7) Uani 1 1 d . . . . .
H1 H 0.4386 0.2834 0.7616 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5100(5) 0.1873(4) 0.8652(5) 0.100(2) Uani 1 1 d . . . . .
H6A H 0.5474 0.1515 0.8210 0.119 Uiso 1 1 calc R U . . .
H6B H 0.5961 0.2167 0.9105 0.119 Uiso 1 1 calc R U . . .
C7 C 0.4422(5) 0.1199(4) 0.9085(4) 0.098(2) Uani 1 1 d . . . . .
H7A H 0.4456 0.1460 0.9685 0.117 Uiso 1 1 calc R U . . .
H7B H 0.4984 0.0575 0.9178 0.117 Uiso 1 1 calc R U . . .
C8 C 0.4184(6) 0.3632(5) 0.8666(6) 0.111(2) Uani 1 1 d . . . . .
H8A H 0.3928 0.3494 0.9227 0.133 Uiso 1 1 calc R U . . .
H8B H 0.3404 0.4069 0.8293 0.133 Uiso 1 1 calc R U . . .
C9 C 0.5630(9) 0.4210(8) 0.8926(8) 0.154(4) Uani 1 1 d . . . . .
H9A H 0.5535 0.4835 0.9230 0.185 Uiso 1 1 calc R U . . .
H9B H 0.6451 0.3820 0.9322 0.185 Uiso 1 1 calc R U . . .
O8 O 0.5835(10) 0.4377(6) 0.8080(8) 0.220(4) Uani 1 1 d . . . . .
N2 N -0.0130(2) 0.15708(15) 0.73426(14) 0.0294(4) Uani 1 1 d . . . . .
H2 H -0.0717 0.2013 0.6852 0.035 Uiso 1 1 calc R U . . .
C12 C -0.0821(3) 0.1643(2) 0.8095(2) 0.0387(6) Uani 1 1 d . . . . .
H12A H -0.0389 0.1138 0.8556 0.046 Uiso 1 1 calc R U . . .
H12B H -0.1896 0.1520 0.7855 0.046 Uiso 1 1 calc R U . . .
C13 C -0.0555(4) 0.2669(2) 0.8528(2) 0.0438(6) Uani 1 1 d . . . . .
H13A H -0.1051 0.3170 0.8078 0.053 Uiso 1 1 calc R U . . .
H13B H -0.0988 0.2700 0.9034 0.053 Uiso 1 1 calc R U . . .
O5 O 0.1015(3) 0.28823(18) 0.88600(17) 0.0422(5) Uani 1 1 d . . . . .
C15 C -0.0289(4) 0.0549(2) 0.6950(2) 0.0466(7) Uani 1 1 d . . . . .
H15A H -0.1338 0.0347 0.6782 0.056 Uiso 1 1 calc R U . . .
H15B H 0.0292 0.0082 0.7407 0.056 Uiso 1 1 calc R U . . .
C16 C 0.0250(6) 0.0516(3) 0.6122(3) 0.0694(12) Uani 1 1 d . . . . .
H16A H 0.0085 -0.0149 0.5852 0.083 Uiso 1 1 calc R U . . .
H16B H -0.0317 0.0992 0.5668 0.083 Uiso 1 1 calc R U . . .
O7 O 0.1825(5) 0.0756(2) 0.6371(3) 0.0876(12) Uani 1 1 d . . . . .
H93 H 0.1947 0.1258 0.6090 0.131 Uiso 1 1 calc R U . . .
C18 C -0.1846(3) 0.37132(17) 0.57826(15) 0.0264(4) Uani 1 1 d . . . . .
O50 O 0.5602(8) 0.2588(7) 0.6732(5) 0.173(3) Uani 1 1 d . . . . .
C50 C 0.567(2) 0.1730(12) 0.6190(11) 0.322(14) Uani 1 1 d . . . . .
H50A H 0.6681 0.1484 0.6353 0.483 Uiso 1 1 calc R U . . .
H50B H 0.5343 0.1910 0.5551 0.483 Uiso 1 1 calc R U . . .
H50C H 0.5014 0.1218 0.6301 0.483 Uiso 1 1 calc R U . . .
H91 H 0.5090 0.4774 0.7749 0.200 Uiso 1 1 d . U . . .
H33 H 0.121(4) 0.271(3) 0.924(3) 0.032(10) Uiso 1 1 d . . . . .
H50 H 0.6198 0.3180 0.6526 0.8(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9614(16) . ?
Cu1 O6 1.9898(19) . ?
Cu1 N2 2.017(2) . ?
Cu1 N1 2.018(3) . ?
Cu1 O5 2.376(2) . ?
O1 C1 1.265(3) . ?
O2 C1 1.243(3) . ?
O3 C18 1.253(3) . ?
O3 H3 0.8200 . ?
O4 C18 1.239(3) . ?
O6 C7 1.405(5) . ?
C1 C2 1.506(3) . ?
C2 C3 1.391(3) . ?
C2 C4 1.392(3) . ?
C3 C4 1.398(3) 3_566 ?
C3 C18 1.513(3) . ?
C4 C3 1.398(3) 3_566 ?
C4 H4 0.9300 . ?
N1 C8 1.459(7) . ?
N1 C6 1.472(5) . ?
N1 H1 0.9800 . ?
C6 C7 1.375(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.496(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O8 1.375(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O8 H91 0.897(11) . ?
N2 C12 1.474(3) . ?
N2 C15 1.477(4) . ?
N2 H2 0.9800 . ?
C12 C13 1.507(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O5 1.423(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O5 H33 0.59(4) . ?
C15 C16 1.488(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O7 1.434(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O7 H93 0.8200 . ?
O50 C50 1.42(2) . ?
O50 H50 1.063(6) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O6 173.27(9) . . ?
O1 Cu1 N2 89.43(8) . . ?
O6 Cu1 N2 96.63(8) . . ?
O1 Cu1 N1 91.05(9) . . ?
O6 Cu1 N1 82.96(10) . . ?
N2 Cu1 N1 178.70(12) . . ?
O1 Cu1 O5 91.49(8) . . ?
O6 Cu1 O5 92.45(10) . . ?
N2 Cu1 O5 80.06(9) . . ?
N1 Cu1 O5 98.71(12) . . ?
C1 O1 Cu1 123.92(16) . . ?
C18 O3 H3 109.5 . . ?
C7 O6 Cu1 112.4(2) . . ?
O2 C1 O1 126.2(2) . . ?
O2 C1 C2 118.5(2) . . ?
O1 C1 C2 115.4(2) . . ?
C3 C2 C4 120.55(18) . . ?
C3 C2 C1 120.84(19) . . ?
C4 C2 C1 118.6(2) . . ?
C2 C3 C4 118.71(19) . 3_566 ?
C2 C3 C18 120.88(18) . . ?
C4 C3 C18 120.4(2) 3_566 . ?
C2 C4 C3 120.7(2) . 3_566 ?
C2 C4 H4 119.6 . . ?
C3 C4 H4 119.6 3_566 . ?
C8 N1 C6 116.8(5) . . ?
C8 N1 Cu1 112.6(3) . . ?
C6 N1 Cu1 107.3(2) . . ?
C8 N1 H1 106.5 . . ?
C6 N1 H1 106.5 . . ?
Cu1 N1 H1 106.5 . . ?
C7 C6 N1 114.1(4) . . ?
C7 C6 H6A 108.7 . . ?
N1 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
N1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 O6 112.7(4) . . ?
C6 C7 H7A 109.0 . . ?
O6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
O6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C9 119.2(6) . . ?
N1 C8 H8A 107.5 . . ?
C9 C8 H8A 107.5 . . ?
N1 C8 H8B 107.5 . . ?
C9 C8 H8B 107.5 . . ?
H8A C8 H8B 107.0 . . ?
O8 C9 C8 101.5(8) . . ?
O8 C9 H9A 111.5 . . ?
C8 C9 H9A 111.5 . . ?
O8 C9 H9B 111.5 . . ?
C8 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
C9 O8 H91 108.8(10) . . ?
C12 N2 C15 111.2(2) . . ?
C12 N2 Cu1 110.66(16) . . ?
C15 N2 Cu1 115.5(2) . . ?
C12 N2 H2 106.3 . . ?
C15 N2 H2 106.3 . . ?
Cu1 N2 H2 106.3 . . ?
N2 C12 C13 110.4(2) . . ?
N2 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O5 C13 C12 110.7(2) . . ?
O5 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 O5 Cu1 103.26(17) . . ?
C13 O5 H33 105(4) . . ?
Cu1 O5 H33 117(4) . . ?
N2 C15 C16 110.6(3) . . ?
N2 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O7 C16 C15 110.1(3) . . ?
O7 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
O7 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C16 O7 H93 109.5 . . ?
O4 C18 O3 125.0(2) . . ?
O4 C18 C3 117.8(2) . . ?
O3 C18 C3 117.3(2) . . ?
C50 O50 H50 108.1(9) . . ?
O50 C50 H50A 109.5 . . ?
O50 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
O50 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 -7.1(4) . . . . ?
Cu1 O1 C1 C2 173.61(15) . . . . ?
O2 C1 C2 C3 122.9(3) . . . . ?
O1 C1 C2 C3 -57.7(3) . . . . ?
O2 C1 C2 C4 -57.9(3) . . . . ?
O1 C1 C2 C4 121.4(2) . . . . ?
C4 C2 C3 C4 0.5(3) . . . 3_566 ?
C1 C2 C3 C4 179.6(2) . . . 3_566 ?
C4 C2 C3 C18 178.9(2) . . . . ?
C1 C2 C3 C18 -2.0(3) . . . . ?
C3 C2 C4 C3 -0.5(3) . . . 3_566 ?
C1 C2 C4 C3 -179.6(2) . . . 3_566 ?
C8 N1 C6 C7 96.7(7) . . . . ?
Cu1 N1 C6 C7 -30.7(7) . . . . ?
N1 C6 C7 O6 37.3(9) . . . . ?
Cu1 O6 C7 C6 -24.8(7) . . . . ?
C6 N1 C8 C9 62.7(9) . . . . ?
Cu1 N1 C8 C9 -172.4(7) . . . . ?
N1 C8 C9 O8 59.1(11) . . . . ?
C15 N2 C12 C13 176.1(2) . . . . ?
Cu1 N2 C12 C13 46.4(3) . . . . ?
N2 C12 C13 O5 -57.4(3) . . . . ?
C12 C13 O5 Cu1 36.4(3) . . . . ?
C12 N2 C15 C16 173.3(3) . . . . ?
Cu1 N2 C15 C16 -59.5(3) . . . . ?
N2 C15 C16 O7 62.6(4) . . . . ?
C2 C3 C18 O4 -46.5(3) . . . . ?
C4 C3 C18 O4 131.9(2) 3_566 . . . ?
C2 C3 C18 O3 134.1(2) . . . . ?
C4 C3 C18 O3 -47.4(3) 3_566 . . . ?

_refine_diff_density_max         1.218
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.100

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

